EP1117652B1 - Tan-1057 derivate - Google Patents
Tan-1057 derivate Download PDFInfo
- Publication number
- EP1117652B1 EP1117652B1 EP99968234A EP99968234A EP1117652B1 EP 1117652 B1 EP1117652 B1 EP 1117652B1 EP 99968234 A EP99968234 A EP 99968234A EP 99968234 A EP99968234 A EP 99968234A EP 1117652 B1 EP1117652 B1 EP 1117652B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- formula
- compounds
- mmol
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 0 CN(C(CNC(N*)=N1)C1=O)C(C[C@@](*)CCCNC(N)=N)=O Chemical compound CN(C(CNC(N*)=N1)C1=O)C(C[C@@](*)CCCNC(N)=N)=O 0.000 description 10
- CHJJGSNFBQVOTG-UHFFFAOYSA-N CNC(N)=N Chemical compound CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N Cc1cc(C)ccc1 Chemical compound Cc1cc(C)ccc1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
Definitions
- (C 1 -C 6 ) alkyl in the above definitions of R 1 and R 4 to R 19 denotes a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, pentyl and hexyl, with (C 1 -C 4 ) alkyl groups being preferred and methyl being particularly preferred.
- Q preferably represents oxygen
- Hal means halogen such as fluorine, chlorine, bromine and iodine.
- Cleavage of the amino protecting group in the conventionally protected amino group A is carried out according to conventional methods (see T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, 2nd edition, John Wiley and Sons, New York, 1991), preferably tert-butyloxycarbonyl with hydrochloric acid in dioxane, Fluorenyl-9-methoxycarbonyl with piperidine and benzyloxycarbonyl by hydrogenolysis in the presence of catalysts such as e.g. with Raney nickel, palladium, Palladium on carbon or platinum or preferably palladium (II) chloride. Possibly Amino protecting groups also present in group Z, e.g. benzyloxycarbonyl can also be split off in this implementation.
- the natural product derivatives of the present invention have interesting pharmacological Effects on.
- the compounds of the present Invention have an antibacterial effect and are therefore in the fight against bacterial infections in humans and animals.
- the known compounds TAN-1057 A and B the problem that the treated Germs quickly become resistant to these compounds and you are the one Considers that the compounds of the present invention are comparable antibacterial activity can lead to resistance formation less quickly.
- Bacteria of the S. aureus 133 strain were found in various concentrations of TAN 1057 A, B incubated for 24 hours. Bacteria found at higher TAN 1057 A, B concentrations showed visible growth, were added to new culture bottles different TAN 1057 A, B concentrations were inoculated and incubated again. This process was repeated over several days and gradually bacteria selected with increased resistance to TAN 1057 A, B.
- Hepatocytes HepG2
- mouse macrophage cells J774.A1
- the mouse macrophage cell line used is a particularly sensitive indicator for toxic effects. All tested derivatives showed less toxicity than TAN 1057 FROM.
- the vitality and functionality of human HepG2 liver cells were checked after treatment with exemplary compounds.
- 2 x 10 4 - 1 x 10 5 cells were incubated in RPMI 1640 (Whittacker) with 10% heat-inactivated fetal calf serum (Gibco) for 40-48 hours at 37 ° C.
- the test substances were contained in the concentrations of 10, 2 and 0.4 ⁇ g / ml in the incubation volume of 200 ⁇ l.
- the S. aureus 133 isolates which are intermediate and highly resistant to TAN 1057 A, B. were tested against the derivatives of the invention.
- the therapeutically active compounds are said to be in the pharmaceuticals listed above Preparations preferably in a concentration of about 0.1 to 99.5, preferably from about 0.5 to 95% by weight of the total mixture.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19838998A DE19838998A1 (de) | 1998-08-27 | 1998-08-27 | Neue Naturstoffderivate |
| DE19838998 | 1998-08-27 | ||
| PCT/EP1999/006124 WO2000012484A1 (de) | 1998-08-27 | 1999-08-20 | Tan-1057 derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1117652A1 EP1117652A1 (de) | 2001-07-25 |
| EP1117652B1 true EP1117652B1 (de) | 2004-05-26 |
Family
ID=7878913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP99968234A Expired - Lifetime EP1117652B1 (de) | 1998-08-27 | 1999-08-20 | Tan-1057 derivate |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6617332B1 (es) |
| EP (1) | EP1117652B1 (es) |
| JP (1) | JP4533535B2 (es) |
| KR (1) | KR20010099629A (es) |
| CN (1) | CN1324348A (es) |
| AT (1) | ATE267816T1 (es) |
| AU (1) | AU759618B2 (es) |
| BG (1) | BG105275A (es) |
| BR (1) | BR9913337A (es) |
| CA (1) | CA2342102C (es) |
| DE (2) | DE19838998A1 (es) |
| EE (1) | EE200100125A (es) |
| ES (1) | ES2219105T3 (es) |
| HK (1) | HK1041884A1 (es) |
| HR (1) | HRP20010135A2 (es) |
| HU (1) | HUP0103316A3 (es) |
| ID (1) | ID28365A (es) |
| IL (1) | IL141325A0 (es) |
| NO (1) | NO20010940L (es) |
| NZ (1) | NZ510153A (es) |
| PL (1) | PL346143A1 (es) |
| SK (1) | SK2622001A3 (es) |
| TR (1) | TR200100637T2 (es) |
| WO (1) | WO2000012484A1 (es) |
| ZA (1) | ZA200101038B (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1113008A1 (en) * | 1999-12-29 | 2001-07-04 | Pfizer Products Inc. | 4-oxo-2-ureido-1,4,5,6-tetrahydro-pyrimidine derivatives useful as antibacterial and antiprotozoal agents |
| US20040204404A1 (en) * | 2002-09-30 | 2004-10-14 | Robert Zelle | Human N-type calcium channel blockers |
| KR20100101073A (ko) * | 2007-12-20 | 2010-09-16 | 닥터 레디스 레보러터리즈 리미티드 | 시타글립틴 및 약제학적으로 허용되는 그의 염의 제조 방법 |
| JP5725561B2 (ja) | 2009-10-15 | 2015-05-27 | 国立大学法人徳島大学 | ジエチレントリアミン五酢酸誘導体の製造方法およびジエチレントリアミン五酢酸誘導体 |
| MY161870A (en) * | 2009-10-16 | 2017-05-15 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| CA2777741A1 (en) * | 2009-10-16 | 2011-04-21 | Rib-X Pharmaceuticals, Inc. | Antimicrobial compounds and methods of making and using the same |
| WO2011047319A2 (en) | 2009-10-16 | 2011-04-21 | Rib-X Pharmaceuticals, Inc. | Antimicrobial compounds and methods of making and using the same |
| WO2011047320A2 (en) | 2009-10-16 | 2011-04-21 | Rib-X Pharmaceuticals, Inc. | Antimicrobial compounds and methods of making and using the same |
| PT2697229T (pt) | 2011-04-15 | 2018-04-13 | Melinta Therapeutics Inc | Compostos antimicrobianos e seus métodos de fabrico e de utilização |
| RU2475479C1 (ru) * | 2011-12-23 | 2013-02-20 | Федеральное государственное бюджетное учреждение Министерства здравоохранения и социального развития Российской Федерации "Медицинский радиологический научный центр" (ФГБУ МРНЦ Минздравсоцразвития России) | Вазоконстрикторное средство |
| EP3038623A4 (en) | 2013-09-09 | 2017-04-19 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| AU2014315050A1 (en) | 2013-09-09 | 2016-03-24 | Melinta Therapeutics, Inc. | Antimicrobial compunds and methods of making and using the same |
| CA2979342A1 (en) | 2015-03-11 | 2016-09-15 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| WO2017193016A1 (en) | 2016-05-06 | 2017-11-09 | Melinta Therapeutics, Inc. | Antimicrobials and methods of making and using same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2873340B2 (ja) * | 1988-04-29 | 1999-03-24 | 武田薬品工業株式会社 | 抗生物質ｔａｎ―１０５７，その製造法および用途 |
| CA2297055A1 (en) * | 1997-08-07 | 1999-02-18 | Research Corporation Technologies, Inc. | Antibiotic for methicillin resistant bacteria |
-
1998
- 1998-08-27 DE DE19838998A patent/DE19838998A1/de not_active Ceased
-
1999
- 1999-08-20 US US09/763,711 patent/US6617332B1/en not_active Expired - Fee Related
- 1999-08-20 AT AT99968234T patent/ATE267816T1/de not_active IP Right Cessation
- 1999-08-20 KR KR1020017002417A patent/KR20010099629A/ko not_active Application Discontinuation
- 1999-08-20 SK SK262-2001A patent/SK2622001A3/sk unknown
- 1999-08-20 ID IDW20010483A patent/ID28365A/id unknown
- 1999-08-20 HU HU0103316A patent/HUP0103316A3/hu unknown
- 1999-08-20 CA CA002342102A patent/CA2342102C/en not_active Expired - Fee Related
- 1999-08-20 CN CN99812643A patent/CN1324348A/zh active Pending
- 1999-08-20 EP EP99968234A patent/EP1117652B1/de not_active Expired - Lifetime
- 1999-08-20 DE DE59909607T patent/DE59909607D1/de not_active Expired - Lifetime
- 1999-08-20 IL IL14132599A patent/IL141325A0/xx unknown
- 1999-08-20 TR TR2001/00637T patent/TR200100637T2/xx unknown
- 1999-08-20 ES ES99968234T patent/ES2219105T3/es not_active Expired - Lifetime
- 1999-08-20 BR BR9913337-7A patent/BR9913337A/pt not_active IP Right Cessation
- 1999-08-20 PL PL99346143A patent/PL346143A1/xx not_active Application Discontinuation
- 1999-08-20 AU AU10099/00A patent/AU759618B2/en not_active Ceased
- 1999-08-20 WO PCT/EP1999/006124 patent/WO2000012484A1/de not_active Application Discontinuation
- 1999-08-20 JP JP2000567514A patent/JP4533535B2/ja not_active Expired - Fee Related
- 1999-08-20 NZ NZ510153A patent/NZ510153A/xx unknown
- 1999-08-20 EE EEP200100125A patent/EE200100125A/xx unknown
-
2001
- 2001-02-07 ZA ZA200101038A patent/ZA200101038B/en unknown
- 2001-02-20 BG BG105275A patent/BG105275A/xx unknown
- 2001-02-23 NO NO20010940A patent/NO20010940L/no unknown
- 2001-02-26 HR HR20010135A patent/HRP20010135A2/hr not_active Application Discontinuation
-
2002
- 2002-05-17 HK HK02103758.4A patent/HK1041884A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ510153A (en) | 2002-12-20 |
| ATE267816T1 (de) | 2004-06-15 |
| HUP0103316A3 (en) | 2002-06-28 |
| BR9913337A (pt) | 2001-05-15 |
| IL141325A0 (en) | 2002-03-10 |
| HK1041884A1 (zh) | 2002-07-26 |
| AU1009900A (en) | 2000-03-21 |
| NO20010940L (no) | 2001-04-23 |
| ES2219105T3 (es) | 2004-11-16 |
| JP4533535B2 (ja) | 2010-09-01 |
| WO2000012484A1 (de) | 2000-03-09 |
| ZA200101038B (en) | 2002-02-07 |
| HUP0103316A2 (hu) | 2002-04-29 |
| PL346143A1 (en) | 2002-01-28 |
| EE200100125A (et) | 2002-06-17 |
| AU759618B2 (en) | 2003-04-17 |
| CN1324348A (zh) | 2001-11-28 |
| KR20010099629A (ko) | 2001-11-09 |
| SK2622001A3 (en) | 2001-11-06 |
| JP2002523496A (ja) | 2002-07-30 |
| US6617332B1 (en) | 2003-09-09 |
| CA2342102C (en) | 2008-10-28 |
| ID28365A (id) | 2001-05-17 |
| TR200100637T2 (tr) | 2001-10-22 |
| DE19838998A1 (de) | 2000-03-09 |
| DE59909607D1 (de) | 2004-07-01 |
| BG105275A (en) | 2001-11-30 |
| HRP20010135A2 (en) | 2002-02-28 |
| CA2342102A1 (en) | 2000-03-09 |
| NO20010940D0 (no) | 2001-02-23 |
| EP1117652A1 (de) | 2001-07-25 |
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